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Lanthanide(III) coordination compounds are employed in several fundamental and applied research fields such as organic synthesis, bioinorganic chemistry, optical and magnetic imaging, catalysis, environment and geochemistry. All these applications have been favoured by the recent developments of a detailed knowledge of fundamental properties (electronic, spectroscopic, thermodynamic, magnetic, structural) of elements, ions and their compounds.Ln3+ are hard acids and present strong affinity for charged ligands or neutral O- and N-donors, as indicated by a wide number of papers concerning formation of their complexes in solution. These studies allowed one to gain information on the complex stabilities, the metal-ion selectivity of a given ligand, the influence of the solvent on the nature and stability of the species in solution. Most of the above studies deal with aqueous solutions, while studies in non-aqueous media are less common. Despite more limited, investigations in aprotic solvents are particularly interesting as they allow one to extend the knowledge on the coordination chemistry of lanthanide(III), disclosing metal-ligand interactions not easily accessible in water due to ligand protonation equilibria, Ln(III) hydrolysis and strong hydration of the cations, which hampers interactions with neutral donors.This review analyzes a wide number of thermodynamic studies concerning formation of lanthanide(III) complexes with selected, simple neutral N-donors (amines, pyridines), O-donors (crown ethers, aza-crown ethers and cryptands) and charged inorganic ligands (halides, thiocyanate, nitrate, perchlorate, triflate) in non-aqueous solvents. The main aim of the review is to face the basic question of what are the factors governing the complex stability and selectivity within the lanthanide series and how are they influenced by different coordinating media. Fundamental properties of Ln ions, such as ionic radii, common oxidation states and structural aspects of their solvates are as well analyzed.Several points emerged from a critical analysis of the papers reviewed:. i)Ln3+ salts used in thermodynamic studies in poor coordinating solvents are often not completely dissociated and, in this case, the data obtained reflect multiple simultaneous equilibria in solution. Comparisons between thermodynamic results in poor and high solvating media must be therefore regarded with caution as they may refer to different reacting metal-species, hence, to different metal-ligand equilibria.ii)High solvating aprotic media can be considered as ideal for thermodynamic studies since lanthanide(III) is only present as Ln(solv)n3+species. However, in this case, the strong solvation of Ln3+ ions hinders complex formations with weak or relatively weak donors.iii)Solvation of lanthanide(III) cations in non-aqueous solutions is generally a major factor in determining the complex stabilities which, for the different kinds of ligands examined, follow the general trend: PC>AN>MeOH>DMF>DMSO.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Several new neutral and cationic organopalladium complexes containing a P-N chelating ligand, 2-(diisopropylphosphinomethyl)-1-methylimidazole, have been synthesized and characterized. The neutral complexes [PdPh(I)(P-N)] 1 and [PdMe(I)(P-N)] 2 have been synthesized by oxidative addition of PhI and MeI, respectively to Pd(dba)2 (dba = dibenzylideneacetone) in the presence of the P-N ligand. The cationic complexes [PdPh(PPh3)(P-N)]BF4 3 and [PdMe(PPh3)(P-N)]BF4 4 were obtained by adding an acetone solution of AgBF4/PPh3 to the corresponding neutral precursors 1 and 2, respectively. A cationic allyl complex, [Pd(eta3-C3H5)(P-N)]Br 5, has also been prepared by oxidative addition of 3-bromopropene to Pd(dba)2 in presence of the P-N ligand. Single crystal structure determinations have been carried out for 1, 4 and 5. Carbonylation of the metal-carbon bond in these new complexes was also studied. The neutral complexes 1 and 2 react smoothly with CO to give carbonylated products [Pd(C(O)Ph)I(P-N)] 6 and [Pd(C(O)Me)I(P-N)] 7, respectively. The methyl complex 2 reacted much faster than the phenyl complex 1. The cationic complexes 3 and 4 are inert and do not give any carbonylated product. However, in the case of the reaction of 3, evidence has been obtained for the formation of a CO-coordinated complex [PdPh(PPh3)(CO)(P-N)]BF4 8 in which the P-N ligand temporarily acts as a monodentate phosphorus-bonded ligand. On the other hand, a cationic complex containing a weakly coordinating acetone molecule, [PdMe{(CD3)2CO}(P-N)]BF4 9, showed an enhanced reactivity toward CO and gave [Pd{MeC(O)}(CO)(P-N)]BF4 10.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Thiazole-containing pi-conjugated moieties are important structural units in the development of new electronic and photochromic materials. We have developed a Pd-catalyzed syn-hydroarylation reaction of diaryl alkynes with thiazoles that provides access to thiazole-containing triarylethylenes. Pd(II) complexes derived from Pd(0) species and carboxylic acids facilitated C-H functionalization of the unsubstituted thiazole with high C5 selectivity. The catalytic system was also compatible with other azoles, such as oxazoles and a pyrazole, allowing the stereoselective syntheses of various trisubstituted olefins.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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4-Substituted O-benzyl benzamide oximes reacted with 2-iodobenzonitrile in the presence of 0.1 mol % of [Pd2(dba)3], 0.2 mol % of XantPhos, and 1.5 equiv of Cs2CO3 in dioxane under argon to give 2-arylquinazolin-4-amines. The described reaction is a new type of cascade processes, which affords 4-amino-quinazoline derivatives without using highly reactive chlorinating agents.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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A phosphine sulfide Pd(II) complex, [Pd(p2S2)2](BF4)2 (1) (p2S2 = 1,2-bis(diphenylphosphino)ethane disulfide), was synthesized and characterized by an X-ray crystal structure analysis and 31P NMR spectroscopy. The p2S2 ligand exchange rate of 1 with free p2S2 in chloroform was revealed to be comparable to the general solvent exchange rate on Pd(II). The catalytic activity of 1 was evaluated by carrying out the Heck reaction. The diminishing of the induction period and acceleration of the reaction were observed for 1 by comparing the phosphine Pd(II) complexes with a leaving chloro ligand, [PdCl(p3)]Cl (p3 = bis[2-(diphenylphosphino)ethyl]phenylphosphine) and [PdCl(pp3)]Cl (pp3 = tris[2-(diphenylphosphino)ethyl]phosphine), and the catalytic activity was comparable to that of the phosphine Pd(0) complex, [Pd(PPh3)4]. Such a high catalytic activity of 1 is attributed to the pi-accepting ability of the phosphine sulfide S atom which stabilizes the catalytically active Pd(0) species electronically and weak sigma-donation of the S atom which does not block the formation and a subsequent reaction of the Pd(II) substrate adduct in the catalytic cycle.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method